How to Date Shy Guys

Co-authored by Moshe Ratson, MFT, PCC

Last Updated: April 21, 2024 Approved

Are you wondering how to take things to the next level with that shy cutie? Shy guys can be perplexing— they may not openly let you know they like you or ask you out, so you'll have to be willing to make the first move in order to date them. Once you've broken the ice, work your magic to get closer to a shy guy. No matter what happens, you'll need to reel in your expectations--a shy guy may be a little different from other guys you've dated.

Part 1

Part 1 of 3:

Taking the Initiative

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1
Show interest in little ways. ^{[1]
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Expert Source

Moshe Ratson, MFT, PCC
Marriage & Family Therapist

Expert Interview. 7 August 2019.} Some shy guys need the green light to know that you're interested. Whenever you see him, be sure to smile and say “hi.” ^{[2]
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- If you see him from across the room, hold eye contact for a little while and smile. Doing so may give him the courage to come over.
2
Approach him one-on-one. Even the most outgoing guys can be overwhelmed when you're constantly surrounded by a group of friends. Take the pressure off by stepping away from your pals to chat him up. ^{[3]
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- A shy guy will be more likely to engage with you one-on-one.
- If your friends are around, ask them to meet you later so you can talk in private. Then walk up to your shy guy with a huge smile and say "Hi."
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Expert Source

Moshe Ratson, MFT, PCC
Marriage & Family Therapist

Expert Interview. 7 August 2019.} Greeting one another and making small talk will only get you so far with a shy guy. Take conversations deeper by using open-ended questions that require more than a “yes” or “no” answer. ^{[5]
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Conversation Starters:
Questions: “That test last week was so hard. How did it go for you?”
“What are your plans for this weekend?”
“What’s the first thing you want to do when school gets out for summer?”
“That t-shirt is so cool! Where did you get it?”
“My week has been crazy. How is yours going so far?”
Tip: Be prepared with casual follow-up questions to keep the conversation going. Show him that you think he’s interesting and that you want to keep talking!
Once you and Mr. Shy get on friendly terms, suggest a time for you to hang out together. These should be low-key get-togethers under “safe” conditions, using something that connects the two of you. ^{[6]
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Easy Ways to Get to Know Each Other:
Hanging out in a relaxed setting: Ask him if he wants to work together in a subject you both have.
Ask him to walk or carpool home together, if you live near each other.
See if he wants to help you set up for an event, like a dance or sports game.
If you work at a restaurant or shop, invite him to visit you there.
Tip: Ask him what he likes to do on the weekends. Choose one of his favorite things to do, like going to a sports event or playing video games, and ask if you can join in!

Part 2

Part 2 of 3:

Building a Connection

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Guys in general are more receptive during shoulder-to-shoulder activities as opposed to head-on ones. Try to reduce the pressure and help him get comfortable with you by talking and doing activities side-by-side. ^{[7]
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Finding a way to sit next to him:
Grab seats together in the car, or on a bus or train.
Go to a diner or restaurant and get seats at the bar or counter instead of a table.
Sit side-by-side at a movie or sporting event.
Volunteer at a bake sale or soup kitchen and serve side-by-side.
Try some light flirting: If it feels right, you can brush his shoulder from time to time or bump his arm with yours. Lean over to look at his phone or playfully steal food off his plate.
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Connect through shared interests. ^{[8]
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Expert Source

Moshe Ratson, MFT, PCC
Marriage & Family Therapist

Expert Interview. 7 August 2019.} Your shy crush will be more relaxed when he's in his “zone,” so find things you have in common. Use these interests to deepen conversations or bring excitement to your time together.
- For example, if you both like Stranger Things, consider binge-watching the show or going to a convention together.
- You're more likely to win him over if the interest is genuinely mutual.
  He'll be able to tell if you're pretending to like something just to get close to him.
Calling it a “date” just might freak out a shy guy in the early stages, so ask him out to lighter, small group gatherings. Maybe ask him to come with you and friends to a concert or a festival happening in your city. ^{[9]
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Small Group Activities:
Things to Do: Head to a concert or festival.
Go to a sports game at your school or get cheap tickets to a pro game.
Host a game night for both of your friend groups.
Invite people who will get along together. Tell your friends what you’re planning and ask if there’s anyone they really dislike that you should avoid inviting. Pulling together a group that gets along will reduce stress for you and your guy.
Don’t overwhelm him with people. Keep these gatherings intimate: just the two of you, 1-2 of his close friends, and 1-2 of yours. This sweet spot will prevent him from feeling anxious at a big group get-together, but won’t make it seem too “date-like” either.
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Up the stakes by hanging out one-on-one. After you've gotten to know one another, initiate plans for a real date. Plan the date around your personalities, so you both feel comfortable. ^{[10]
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- Consider going to a movie for a first date with a shy guy, because there's no pressure to talk or make face-to-face chit-chat.
- If he's not the mushy type, resist the urge to plan a romantic candlelight dinner. Instead, go for something light-hearted and casual, so you can both be yourselves.

Part 3

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Advancing the Relationship

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1
Get comfortable with some silence. At first, you might be unnerved by the many silences that come with dating a shy guy. You might need to
repeat something to yourself, like “Silence is not a bad thing” to avoid rushing in with empty or unnecessary conversation.
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- Over time, you might find that you enjoy the shared silences between you—it can be a relief to not always have to talk!
- Silence is perfectly okay and natural in relationships.
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Give him space as needed. If your boyfriend is shy or introverted, he may need time alone to recharge. Don't take this personally—it's nothing against you. Just establish a way for him to let you know when he needs a little space. ^{[12]
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- He might put on some headphones when you're together to demonstrate a need to pull away. Or, he might grow quiet and withdrawn.
- If this happens, you might ask, "Why don't I go in the other room and give you some space?" or "I think I'll go hang out with my friends for a while. Call ya later, okay?"
3
Allow him time to warm to your friends. Avoid situations in which your friends "grill" him with questions. This might make him retreat back into his shell. Also,
ask him in advance if he's okay hanging out with a group of your pals.
He may feel more comfortable if he can bring a friend along, too.
- Remember, just because you love your friends doesn't mean your guy will. Give him some time to warm up to them instead of assuming that he'll like them since he likes you.
4
Don't draw attention to his shyness. You might think it's cute when your crush acts shy or blushes, but he may be mortified inside. Avoid calling out his shyness, whether in a group or when you're alone. Just overlook it and act like whatever he's doing is totally normal. ^{[13]
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- For example,
  never say “Aww, you're really shy!” or “You're blushing!”
- Calling attention to his shyness will make him feel self-conscious and maybe make him not want to hang out with you.
One of the tough things about dating a shy guy is having to initiate intimacy. Hugs, kisses, and other forms of affection will likely have to be prompted by you in order for them to happen. Your guy may be too shy to make the first move. ^{[14]
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Tips for Creating Intimacy:
Start slow. Nudge your hand into his while you’re walking alongside each other, or open your arms for a hug when you greet him. If he’s hesitant, kiss him on the cheek at the end of your first few dates.
Ask before you make a new move. This might sound awkward, but it’s not! You can say softly, “I really want to kiss you right now. Is that ok?” It’s important that you get consent when you’re both clear-headed and sober, so you can be sure that he wants this too.
Don’t worry about possible rejection. If you’ve been spending lots of time together, your guy will be thrilled to take things to the next level. Once he gets comfortable, he might even take the lead, too.
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Expert Source

Moshe Ratson, MFT, PCC
Marriage & Family Therapist

Expert Interview. 7 August 2019.} Dating a shy guy might feel agonizing. You might constantly wonder if you're on the right track. You might also get frustrated when it takes him longer to open up. He will send you signals in his own way to let you know that he's into you. Give it time. ^{[16]
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Expert Q&A

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Question

How can I impress a shy guy?

Moshe Ratson, MFT, PCC
Marriage & Family Therapist
Moshe Ratson is the Executive Director of spiral2grow Marriage & Family Therapy, a coaching and therapy clinic in New York City. Moshe is an International Coach Federation accredited Professional Certified Coach (PCC). He received his MS in Marriage and Family Therapy from Iona College. Moshe is a clinical member of the American Association of Marriage and Family Therapy (AAMFT), and a member of the International Coach Federation (ICF).

Moshe Ratson, MFT, PCC

Marriage & Family Therapist

Expert Answer

Try making the first move and letting him know that you're interested right away. That way, he may be more inclined to open up to you.

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How can I get a shy guy to open up?

Moshe Ratson, MFT, PCC
Marriage & Family Therapist
Moshe Ratson is the Executive Director of spiral2grow Marriage & Family Therapy, a coaching and therapy clinic in New York City. Moshe is an International Coach Federation accredited Professional Certified Coach (PCC). He received his MS in Marriage and Family Therapy from Iona College. Moshe is a clinical member of the American Association of Marriage and Family Therapy (AAMFT), and a member of the International Coach Federation (ICF).

Moshe Ratson, MFT, PCC

Marriage & Family Therapist

Expert Answer

It takes some time for shy people to get comfortable around others, so be patient and try to ask open-ended questions to get him to talk more.

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Question

How do you make a shy guy fall in love with you?

Klare Heston, LCSW
Licensed Social Worker
Klare Heston is a Licensed Independent Clinical Social Worker based in Cleveland, Ohio. With experience in academic counseling and clinical supervision, Klare received her Master of Social Work from the Virginia Commonwealth University in 1983. She also holds a 2-Year Post-Graduate Certificate from the Gestalt Institute of Cleveland, as well as certification in Family Therapy, Supervision, Mediation, and Trauma Recovery and Treatment (EMDR).

Klare Heston, LCSW

Licensed Social Worker

Expert Answer

You can't really "make" someone fall in love with you, but you can be very clear about your interest in them. Make it a point to talk with him whenever you can; pick up on his interests or hobbies and talk about them; attend events that you think he attends; be willing to tell him that you like him and would like to spend more time together. This can take a lot of the risk out for him.

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Moshe Ratson, MFT, PCC
Marriage & Family Therapist

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How to Date Shy Guys

Steps

Taking the Initiative

Building a Connection

Advancing the Relationship

Expert Q&A

Tips

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